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Updated: May 17, 2026

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
Published on: December 23, 2016
Synthesis of donor-σ-perylenebisimide-acceptor molecules having PEG swallowtails and sulfur anchors
Rajesh Kota1, Ramakrishna Samudrala, Daniell Lewis Mattern
1Department of Chemistry and Biochemistry, University of Mississippi, P.O. Box 1848, University, Mississippi 38677, United States.
Abstract:
Donor-σ-Acceptor (D-σ-A) molecules, arrayed in a monolayer between electrodes, can serve as molecular rectifiers. Using perylene-3,4,9,10-tetracarboxylic bisimide (PBI) as the acceptor allows the attachment of the donor group to one imide nitrogen and a solubilizing swallowtail, normally a long (e.g., C(19)) alkane connected at midchain, on the other. Such an alkyl tail facilitates the formation of Langmuir-Blodgett (LB) monolayers. We have employed several modified swallowtails to make new D-σ-A molecules: poly(ethylene glycol) (PEG) swallowtails with 6 ether oxygens or with 4 ether oxygens to promote hydrophilicity in orienting LB monolayers, and alkyl swallowtails ending with sulfur anchors (thioacetate, thiol, or methyl disulfide) to stabilize attachment of the D-σ-A molecules to gold electrodes. The preparation and characterization of D-σ-A molecules containing combinations of these swallowtails with pyrene, ferrocene, and tetramethylphenylenediamine donor groups is described.
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